4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidine | 577968-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidine
• 英文别名: 4-[3-Cyclopentyloxy-4-(difluoromethoxy)phenyl]piperidine-4-carbonitrile
• CAS: 577968-68-4
• 化学式: C₁₈H₂₂F₂N₂O₂
• 分子量: 336.382
• InChiKey: JNRDVRQSUTYTJK-UHFFFAOYSA-N

物化性质

• 沸点：
  468.1±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidine 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 {4-cyano-4-[3-(cyclopentyloxy)-4-(difluoromethoxy)phenyl]piperidine-1-yl}acetic acid
  参考文献：
  名称：

  Highly potent PDE4 inhibitors with therapeutic potential

  摘要：

  Based on the hypothesis that the dose-limiting side effects of PDE4 inhibitors could be mediated via the central nervous system (CNS), design and synthesis of a hydrophilic analogue is considered to be one approach to improving the side-effect profile of Ariflo(TM) 1. Water-soluble piperidine derivatives were found to possess therapeutic potential. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.087
• 作为产物：
  描述：

  (3-cyclopentyloxy-4-difluoromethoxyphenyl) acetonitrile 在 茴香硫醚 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidine
  参考文献：
  名称：

  Highly potent PDE4 inhibitors with therapeutic potential

  摘要：

  Based on the hypothesis that the dose-limiting side effects of PDE4 inhibitors could be mediated via the central nervous system (CNS), design and synthesis of a hydrophilic analogue is considered to be one approach to improving the side-effect profile of Ariflo(TM) 1. Water-soluble piperidine derivatives were found to possess therapeutic potential. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.087

文献信息

• Piperidine derivative compounds and drugs containing the compounds as the active ingredient
  申请人：Ochiai Hiroshi

  公开号：US20050080107A1

  公开（公告）日：2005-04-14

  A piperidine derivative of formula (I) (wherein all symbols are as described in the specification.) and an intermediate for the preparation thereof. The compound of formula (I) has phosphodiesterase 4 inhibitory activity, and it is useful for the prevention and/or treatment of inflammatory diseases, diabetic diseases, allergic diseases, autoimmune diseases, ocular diseases, osteoporosis, bone fracture, osteoarthritis, obesity, bulimia, depression, Parkinson's disease, dementia, ischemia-reperfusion injury, leukemia, acquired immunodeficiency deficiency syndrome (AIDS), shock, systemically inflammatory responsive diseases (SIRS), etc.

  公式（I）的哌啶衍生物（其中所有符号如说明书所述）及其制备的中间体。公式（I）化合物具有磷酸二酯酶4抑制活性，可用于预防和/或治疗炎症性疾病，糖尿病性疾病，过敏性疾病，自身免疫性疾病，眼部疾病，骨质疏松症，骨折，骨关节炎，肥胖症，暴食症，抑郁症，帕金森病，痴呆症，缺血再灌注损伤，白血病，获得性免疫缺陷综合症（AIDS），休克，全身炎症反应性疾病（SIRS）等。
• PIPERIDINE DERIVATIVE COMPOUNDS AND DRUGS CONTAINING THE COMPOUNDS AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1481969B1

  公开（公告）日：2011-01-19
• US7425567B2
  申请人：——

  公开号：US7425567B2

  公开（公告）日：2008-09-16
• Highly potent PDE4 inhibitors with therapeutic potential
  作者：Hiroshi Ochiai、Tazumi Ohtani、Akiharu Ishida、Kensuke Kusumi、Masashi Kato、Hiroshi Kohno、Katuya Kishikawa、Takaaki Obata、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmcl.2003.09.087

  日期：2004.1

  Based on the hypothesis that the dose-limiting side effects of PDE4 inhibitors could be mediated via the central nervous system (CNS), design and synthesis of a hydrophilic analogue is considered to be one approach to improving the side-effect profile of Ariflo(TM) 1. Water-soluble piperidine derivatives were found to possess therapeutic potential. (C) 2003 Elsevier Ltd. All rights reserved.